


femme.

by angelcult



Category: Supernatural
Genre: Boys in Skirts, Fantasy Sex, Feminization, Kink Discovery, Kink Exploration, Masturbation, Mild Daddy Kink, Sensitive Sam Winchester, sam is about sixteen
Language: English
Status: Completed
Published: 2020-01-05
Updated: 2020-01-05
Packaged: 2021-02-27 08:08:21
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,112
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22123855
Author URL: https://archiveofourown.org/users/angelcult/pseuds/angelcult
Summary: Sam’s pretty in stolen panties, but he wonders how far he’d go for that solo high.
Comments: 4
Kudos: 41
Collections: SPN Kink Bingo





	femme.

Sam found that genuinely enjoyed feeling pretty, he enjoyed it when he felt soft and pure. 

Being sixteen and in-between that gawky phase of long limbs and baby fat, Sam found that idealistic want of feminine beauty to be hard to come by, even if he shaved himself bare or wore a pair of stolen lace panties.

There was nothing that really seemed to  _ fit  _ until suddenly, there was.

—

Standing beside Dean as he flirted with the cashier instead of buying their items, Sam allowed his eyes to roam, casual people watching (or as casual as it could be, his training had him alert and cataloguing everything he could) when his eyes stopped dead on a woman whose back was to him.

She had mile long legs, dark and wrapped in fishnet, and further up a leather skirt but what  _ really  _ drew Sam in was when she turned around and revealed that instead of a shirt finishing off the outfit, it was a  [ leather harness ](https://m.beautifulhalo.com/sexy-pentagram-shape-hollow-out-plain-crisscross-harness-bra-top-p-313633.html?curSize=One-Size&showColor=Black&currency1=USD&track=PA_G_SUS227&gclid=CjwKCAiA6bvwBRBbEiwAUER6JTl0pJjDQN4TwJSOo3mdeGgA5NOPNmBoRnbUFutCdzRgLNJpdM01cRoC7rEQAvD_BwE) in the shape of a pentagram and black bra.

Sam flushed and averted his eyes, but he couldn’t ignore the  _ jolt  _ he’d felt. Would he look pretty in something like that?

He thought that maybe he would, but he also knew his chances of actually acquiring the harness were next to none, it wasn’t like he could just  _ ask  _ his father or Dean to buy it, or god forbid, try and order it for himself.

So, he settled for what he could either buy or steal, fishnets and a bra and a skirt, if he was lucky. 

As Dean and Sam settled into the car, Dean tossed him a teasing smirk and Sam frowned, associating the look with trouble, especially given that Dean wasn’t exactly known for  _ not  _ being troublesome in one way or another.

“So, Sammy-“

“It’s Sam.”

Dean kept talking as if he wasn’t interrupted, starting up the car, the engine purring to life beneath them. 

“That girl you were eyeballing, you think she’s hot? Never thought you’d be one of those whips and leather types.” He teased and Sam flushed, burying his head in his hands.

“That’s-that’s  _ not  _ what I was doing-“ And if Sam did, by any chance at all, find himself into things of that nature, it’s not like he was planning on mentioning that to his jerk of a brother anytime soon.

He’d never hear the end of it.

“Oh? So, you often give heart eyes to random strangers?” Dean asked sarcastically, driving the impala was skilled ease and practice as his brother went through multiple stages of mortification in the passenger seat.

He hadn’t even looked at her face, to caught up in the pipe dream of how the fishnets would feel up against his legs, of a skirt rubbing against his dick, tenting up as he got hard-

Sam promptly slammed the door shut on that train of thought, not sure he wanted to get hard in the same car as brother while he was teasing him, there was no doubt in his mind that Dean would think it was because he’d found that girl  _ attractive. _

“No, Dean, I- you’re such a jerk.” It was a weak comeback and they both knew it, but Dean just gave him another teasing look and went back to driving in relative silence, Motley Crüe blaring through the speakers. 

—

Sam found that he wasn’t getting many chances to sneak off to a thrift store (because at least he could  _ buy them  _ that way) or anything of the sort, and he found himself wondering when their next trip to one would be.

He got his reprieve two towns later, while John was hunting a rugaru and after Sam and Dean found most of their clothes to be torn and/or bloodstained, a trip was arranged and Sam was more than grateful, for clothes that  _ weren’t _ from Dean, and therefore, either too big or too short with Sam’s new height. 

The fishnets were surprisingly easy to find in a tub of mismatched socks, fitting easily into his pocket but Sam found that the skirt, that may have been a problem.

He couldn’t find one that he thought he’d like, or one that he could easily sneak into his jacket pocket without a visible bulge. 

Grumbling to himself, Sam kept an eye out on his brothers who were a few aisles away, as well as on any stragglers who might catch him in the act when a snatch of white caught is eye. 

It was a silky, soft thing. Small, with an elastic waist, but looked a bit on the shorter side. Tracing it over, Sam found that he would enjoy the feel of it against his legs.

Giving another cursory glance around, Sam claimed the skirt as his.

—

Being alone, it wasn’t a rarity for Sam but he didn’t ever enjoy it, he was usually too busy worrying about Dean and Dad and what limbs they might be missing when they came back. (When, not if, Sam had to keep that faith, it’s what he prayed for every night.)

Now, however, Sam had something to look forward to besides worry and homework and research. He’d hidden the skirt and fishnets at the bottom of his bag, living on a prayer that Dean didn’t decide to just rummage through it, as he tended to do for the sake of being annoying (which lead to some pretty awkward moments of Dean discovering panties that Sam  _ definitely  _ lied about). 

He found that his prayers must’ve been going through because Dean left his things alone and no one suspected a thing. 

When Dad loaded his brother into the car, Sam had to really push down his excitement, and if his father suspected anything, he didn’t say it.

“Keep the salt lines up, don’t answer the door for anyone. Watch yourself, Sam.” John has been reciting the words since Sam could remember, either directly to him or to Dean. 

His gray eyes softened for a moment as he patted Sam’s shoulder and was out of the door without a backward glance. 

Listening to the impala as the engine roared to life and left the driveway of the house they were in, Sam felt a sigh of relief leave him. The excitement he’d been pushing down quickly took root and thrummed through him.

Glancing around, as if to confirm that he was, in fact, alone, Sam scurried off to his room and immediately began to rummage through his duffle, grabbing the garments he kept carefully hidden from his brother and father. 

The skirt still felt silky and smooth in his hands, soothing his skin as he rubbed over it. The fishnets looked like they would be fairly easy to get on if he didn’t accidentally get his toes stuck in any of the holes and, with his luck, rip it. 

Ladened with clothes, Sam locked himself in the bathroom. The bathroom was larger than many of the ones he’d seen in the different places they lived, and he was grateful for the space.

Looking in the mirror for a brief moment, Sam averted his eyes and stared down at the clothes in his arms. Rather suddenly, he realised he had no idea what came first, the panties or the fishnets?

Taking a risk, since no one was actually going to  _ see him,  _ Sam pulled the fishnets on first and shivered when he felt it against his skin. It was a weird sensation, but they didn’t rub him wrong as he pulled them up, followed by the underwear and lastly, the skirt. 

Sam never did manage to get a bra, so he was shirtless as he examined himself in the mirror.

As he expected, the feel of the skirt against his legs was pure bliss, and it made his face flush. He didn’t really have feminine hips, but the skirt hugged him tightly and Sam very much enjoyed the thought of.. Pretending. 

Sam  _ knew  _ he wasn’t straight, and he wasn’t going to mention it to his father or brother anytime soon either, but he was alone now, with who knows how much time, and he bit his lip. 

His hands slipped between his legs and he pushed down, pushing his hips up and into his palms, moaning softly under his breath. 

The words were on the tip of his tongue, if he said them, he’d cross a line he wasn’t sure he could go back over but.. he was alone, no one else had to know, it wasn’t like he often broadcast his fantasies to the rest of the household (but Dean did say that he talked in his sleep).

Grinding his hips faster, Sam slipped down to his knees and leaned back against the door.

Looking down, Sam saw his cock tenting up the skirt, the bulge not as noticeable through the underwear and the fishnets. 

Biting his lip, Sam lifted his hips and slid the panties down his legs and gasped softly once that little bit of pressure was gone, could feel the press of the fishnet, he found that he loved the feel of it already.

Keeping his hands over the skirt, Sam rutted into his palms, moaning softly, though he wasn’t getting as much friction as he would have liked, his cock strained against the tights and slipped effortlessly against the silk. 

Grunting, Sam twisted onto his knees with his ass in the air as he spoke, rambled words that tended to flow out of him when he was horny and excited. 

“ ‘M so wet, like a-like a girl- _ oh fuck. _ ” Biting into his lip, Sam slid a hand under his skirt, pushing the fishnets down as best he could while trying to get a firm grasp of himself. 

He was leaking  _ a lot,  _ all gathered at the tip, dripping down his fingers when he stroked just once. 

Sam had always been particularly sensitive, and now that he was indulging himself and not getting off as quickly as he usually would, he wasn’t sure if he  _ would  _ last long. 

Repositioning himself again, Sam ended up on his back, legs spread wide. He trailed his fingers over the head, felt himself twitch from even a minuscule amount of pleasure. 

Sam knew himself, knew that he hated saying vulgar words, but he knew that he wouldn’t mind hearing them, wouldn’t mind an imaginary voice growling into his ear as he touched himself.

_ “Such a pretty girl, so wet for me too. Soaking your panties for me.” _

Sam gasped, tilting his head back and thrusting up into his palm, squeezing just a little.

_ “Gonna touch your clit for me?” _

Sam’s eyes shot open and he gripped the base of his dick, nearly coming from  _ imaginary  _ words from a voice he’d probably heard of a hunt or something. 

“It was pretty hot though..” Sam mumbled, sliding his hand up and only touching the head of his cock, mouth open in a small gasp as he did so. 

It was sensitive to the touch, red from Sam’s light teasing, slick with pre-cum. Gripping only the head, Sam palmed it and grinded into his hand, eyes rolling back at the sheer sharpness and overwhelmingly deep pleasure. 

It made him shaky and he hadn’t even come yet.

_ “You gonna cum, girly? I haven’t even fucked that pretty pussy yet.” _

“Fuck! Fuck, yes- I know, I know, I’m sorry, it’s-it’s so sensitive though, feels so good..”

_ “What’s sensitive? Tell me, baby girl, what’s making you shake like that?” _

Sam’s cheeks were red, he could say it, he could, it embarrassed him just as much as it turned him on. 

“My..” His hand slowed, grinding the heel of his hand into the head while his other hand held his cock, grip tight. A harsh whimper forced its way up Sam’s throat at the slowness of his own motions. 

_ “You’re what?” _

“My.. my clit, so sensitive when you make me touch it like that,” Sam’s voice cracked and he arched his back, toes curling as his hips bucked, his pleasure spiking. 

“Wanna cum, can I cum? Please, oh please, please.. You can, you can fuck my- my pussy after, just..”

_ “Greedy girl. Go on, squirt for me. Cum for Daddy.” _

Sam cried out, loud, his moans echoing in the bathroom as he came into his hand, fucking his hips up, and kicking his legs out. It was  _ so much,  _ it made him quiver and gasp, a warmth pooling over him when he finally caught his breath. 

The aftershocks trembled through him, the muscles in his legs still jumped and twitched.

Staring down at his spend covered hands and stomach, Sam swore.

Another kink to add to the list.


End file.
